The University of Chicago, often just called U Chicago, is a private research university in the Windy City. The university is famous for its rigorous academics and generally quirked-up student body. While you won’t find big parties or tailgates at U Chicago, the school is a favorite for students who are looking for deep conversations and social scene that isn’t centered on huge ragers.
The school is notoriously hard to get into. For the Class of 2027, they had just a 4.7% acceptance rate. U Chicago asks a lot of applicants, including a long and relatively challenging application supplement. It is one of the most unusual college supplements, so we wanted to help by breaking it down.
Bizarrely, U Chicago doesn’t have word counts for their prompts. However, they just say your answers should be “1-2 pages each.” This is annoying and a little pretentious, as a lack of a word count can leave a student feeling they unsure or wrong. Rest assured, as long as your supplement is 1-2 pages, you’re going to be fine. But perhaps U Chicago could be like basically every other college and just give a word count. Use a normal font, size and spacing. We trust your best judgment, but if you have questions about formatting, we would be happy to help. Reach out here.
The first question is required for all applicants and is surprisingly straightforward.
Question 1 (Required)
How does the University of Chicago, as you know it now, satisfy your desire for a particular kind of learning, community, and future? Please address with some specificity your own wishes and how they relate to UChicago.
The name of the game here is research, research, research before you even start this essay. You want to be able to speak about the specific opportunities at U Chicago that have led you to apply. This essay might seem tricky, but all it really asks is, " Why do you want to go here?” We have a little bit of a formula we use for this kind of question.
First, you want to introduce what you want to study with a short personal story about how you fell in love with the subject. For example, if you want to study art history, it could be visiting the museum with your grandmother. If you want to study poli-sci because you hope to run for office one day, maybe it was the summer you spent phone banking. Tell a good story and share why you are passionate about it. Then state that it is what you want to study at U Chicago.
Then, it is time to back it up with specifics. You should name at least 2 classes at a higher level (aka not Intro 101 courses) and explain why these classes are perfect for you. Connect them to things you hope to learn, have already explored partially in your studies, and/or how they will help you with a learning or professional goal. You should do the same with a professor you hope to work with. Connect their research to your interests. Don’t be afraid to get nerdy here.
This essay is long. In your research, if you find any U Chicago-specific academic opportunities that speak to you, write about them. Do they offer any unique class types? What about their core classes? Research opportunities? Guiding principles? The more specific here, the better and remember to tie everything you mention back to you and your passions.
Once you have covered academics, you can speak to campus life and extracurricular opportunities. Don’t say, “It is a beautiful campus.” Most schools have beautiful campuses, and this does nothing to illustrate the overlap between you and U Chicago; dig deep and speak to specifics of campus life. We recommend mentioning at least one club that connects to something you are already doing extracurricularly (because then you get to talk about yourself.) For example, if you are on your school’s dance team, you could talk about auditioning for the U Chicago Swing Dance Society. You want to show the overlap between who you are now and who you would be on campus.
If you have future goals, plans, or aspirations, connect them to what you hope to accomplish at U Chicago. Remember, it is all about overlap and specifics. Pretty much you want to leave them with the idea that you would be a perfect fit for U Chicago and U Chicago would be a perfect fit for you.
The second question is where the creativity has to come in. They give you several options to choose from. While they are all out-there, some are better than others. Let’s break them down.
Essay Option 1
We’re all familiar with green-eyed envy or feeling blue, but what about being “caught purple-handed”? Or “tickled orange”? Give an old color-infused expression a new hue and tell us what it represents.
– Inspired by Ramsey Bottorff, Class of 2026
While we like this question more than some others, it is hard because it doesn’t really evoke a 1-2 page response. You are going to have to stretch your answer without it feeling thin. The best way to do this is to tell a good story about how this expression and its color have manifested in your life.
There are a couple of steps you should take before diving into this essay. While there are a couple of ways to start, the easiest is probably choosing the expression you want to play with first. Expressions to get you brainstorming could include:
Once in a Blue Moon
Being in the Red
Green Lit
Paint the Town Red
Grey Area
Black Sheep
White Lie
Blue Blood
Rose Colored Glasses
Don’t be afraid to research the origin of these phrases. You shouldn’t approach this like a research paper, but fully understanding the original phrase will help you twist it. It will also help you avoid expressions that have racist legacies, such as “white trash” or “Yellow Peril.”
Next, brainstorm a new take on the saying. It should feel personal and connect to you in some way. It isn’t enough to just define it; you have to make us care about your usage. For example, maybe you write about taking care of your grandmother and the lazy afternoons spent with your cousins on her brown carpet… or “the Brown Carpet treatment” because those memories are more valuable than a red carpet. It should feel personal and like a story.
This one also opens the door for personal or cultural conceptions of color theory. For example, maybe your mom is Egyptian and thus thinks of Yellow as a mourning color, while your American dad thinks it is cheery, like a smiley face. How would that, excuse us for the pun, color your perception? Maybe you could talk about the “Yellow Area,” which you see as being in-between cultures and navigating differences in your house. Really explore the story; don’t just define the expression.
Essay Option 2
"Ah, but I was so much older then / I'm younger than that now” – Bob Dylan. In what ways do we become younger as we get older?
– Inspired by Joshua Harris, Class of 2016
Okay, so this is probably our least favorite question. These essays are supposed to be creative, but this one doesn’t allow for much creativity. It honestly feels a little schmaltzy, and we generally don’t love it when colleges ask you to respond to a quote from a famous person who has nothing to do with the school. (BTW: Dylan went to U Minnesota… and famously dropped out.)
That said, if you feel pulled to this question, make sure it captures who you are now. Many students tend to only want to talk about their childhood self, and colleges don’t really care about who you were when you were 5… they want to know about you today. This question is especially tricky because to answer this, we need to know about both versions of you while focusing on who you are now. Ideally, this would look something like getting over a middle-school-need to be cool and discovering a love for something seen as childish, such as dinosaurs. It is a fine answer; it just doesn’t scream creativity, and would bet that good answers to this question will sound boringly similar.
Essay Option 3
Pluto, the demoted planet. Ophiuchus, the thirteenth Zodiac. Andy Murray, the fourth to tennis's Big Three. Every grouping has something that doesn’t quite fit in. Tell us about a group and its unofficial member, why (or why not) should it be excluded?
– Inspired by Veronica Chang, Class of 2022
The big misstep here is not connecting it to yourself. Without a personal connection, this answer will quickly become something akin to a Cracked Article or YouTube deep dive, which isn’t ideal. This is another question that doesn’t really need 1-2 pages to answer if you don’t expand on it on your own. You need to add “you” to your answer. Think about the groupings that you are genuinely passionate about.
If you are talking about BBQ sauce and why it should be included amongst Ketchup, Mustard, Relish, and Mayo at the hot dog bar, we need to know why you care so much. Is it because your mom always served it? Is it because you feel like the BBQ sauce in your own friend group? If so, how?
The other trick here is that the question doesn’t really define what a “grouping” is. In their own examples, they have something that was originally part of the group that was taken out for scientific reasons; a common misnomer between astrological signs and constellations; and a men’s tennis term used from 2008 to 2017. These are kind of all over the place, which makes this question more complicated to answer but may allow for more creative answers. Really take time to brainstorm interesting groupings that also speak to something in your life before taking on this question.
Essay Option 4
"Daddy-o", "Far Out", "Gnarly": the list of slang terms goes on and on. Sadly, most of these aren’t so "fly" anymore – “as if!” Name an outdated slang from any decade or language that you'd bring back and explain why you totally “dig it.”
– Inspired by Napat Sakdibhornssup, Class of 2028
They weirdly have multiple essays about expressions this year, and we prefer the other one. However, this can be an interesting one to tackle, especially if you are interested in history, linguistics, and/or creative writing.
The first step is to choose an outdated saying. Don’t use one that appears in the question. Most listed above are from the late 1900s; don’t be afraid to bring back something from farther back. Middle English, anyone? If you speak another language, the slang doesn’t have to be from English. However, make sure you understand the full context of the phrase no matter what language it comes from (honestly, a lot of old slang is pretty racist… make sure you look into it.)
However, remember, you need to bring in more to this answer than just a dictionary definition and overall vibe that words are good. You “could” answer this in two sentences (‘I think we should bring back ‘Copacetic’ because there is no positive phrase for mid anymore. I think it would be helpful to have one.’) But remember, this is supposed to be 1-2 pages. You need to make it personal. Why and how would you use the phrase? Tell us a good story. Think, talking about how your parents don’t understand your “copacetic” relationship with your sister, but you value how lowkey the vibes are between you. Paint us the whole picture.
Essay Option 5
How many piano tuners are there in Chicago? What is the total length of chalk used by UChicago professors in a year? How many pages of books are in the Regenstein Library? These questions are among a class of estimation problems named after University of Chicago physicist Enrico Fermi. Create your own Fermi estimation problem, give it your best answer, and show us how you got there.
– Inspired by Malhar Manek, Class of 2028
This is a really hard question, which could lead to a great essay, but there are many missteps here. That being said, if you want to take it on, step one is to look up “Fermi Problems” or “order-of-magnitude problems.” You should understand the concept you are writing about well. This is a weirdly dark question, given that “Fermi questions” come from his work on the atomic bomb. But sure, tell us about the Regenstein Library, there are people that died, Kim!
Fermi questions come from physics and engineering, but they aren’t questions that can actually be solved by common math or information. This makes them just a little bit philosophical. So don’t expect to be able to look up the books and their page numbers. That isn’t the point. The point is to estimate creatively.
Similarly, this question isn’t all about getting your number perfectly right; it is about your approach. If you can check your final answer, it isn’t a Fermi estimation. Your question should be hard enough, for you really have to put in the work to find the solution. You also want to connect your Fermi problem to your passions and lived experience. To answer this question right, we have to know why you care about the answer you are working toward.
Essay Option 6
And, as always… the classic choose your own adventure option! In the spirit of adventurous inquiry, choose one of our past prompts (or create a question of your own). Be original, creative, thought provoking. Draw on your best qualities as a writer, thinker, visionary, social critic, sage, citizen of the world, or future citizen of the University of Chicago; take a little risk, and have fun!
Usually, we love a “make up your own” prompt. We advise all of our students to use a similar prompt for the Common App essay. However, in this case, we advise doing one of the ones above. U Chicago’s supplement is so specific and gives you questions they are proud of. It is hard to create a prompt that fits in with their other questions… trust us, do one of the above.
U Chicago really pushes their applicants to be creative. Creativity takes time. Don’t try to rush this supplement. It will require brainstorming and editing, as well as taking a good amount of time to write something you can be proud of. If that all sounds too much, we can help.
Get the expert treatment; reach out here.